Old Town

Chicago, Illinois


Old Town is a centrally located, yet residential enclave for those who have tired of the constant bustle of River North but aren't yet ready to retreat to the more suburban-like streets of Lincoln Park. Bordered by these affluent neighbors and the equally illustrious Gold Coast, Old Town is similarly upscale but promises a distinct historic charm. Victorian-style townhomes, brick buildings, and brownstone walk-ups line the residential pockets (which there are a lot of) while the busier main roads boast every convenience you could possibly need. The west side of the neighborhood has all your mainstream shopping (think Whole Foods and Target) while more local haunts tend to dominate the area as you make your way east toward the lake. Wells Street is the unofficial center of the neighborhood and your destination for an array of eateries, cafes, and shops, as well as the home of the renowned Second City comedy theater.

Homes in Old Town

Where To Live

A historic district of Chicago, Old Town is home to some of the most beautiful Victorian-era buildings in the city. Many have been updated with modern amenities but still retain their old-school charm. Farther east, the neighborhood transitions to more high-rise buildings near the lake, while on the west side of Old Town, cozier brick buildings make up the residential area.

Price Vibes

Unlike its closest neighbors, Old Town truly has housing options for every price point. However, if you have a more modest budget and dreams of a historic Victorian, you might be out of luck. Most of Old Town's affordable options are condo units in the handful of high-rise buildings that occupy the east side of the neighborhood, while units in quaint walk-ups tend to fetch a higher price point. If you are looking for a single-family home, be prepared to pay handsomely, though you'll still be better off than you would be looking at a Gold Coast mansion.

Around Old Town

Where To Eat

Wells Street is home to many of Old Town's popular bars and restaurants, including everything from sushi to upscale Italian to classic bar burgers. Even the more casual options are still fairly trendy, offering a more metropolitan ambiance to an evening out.

Friday Night Fun

Grab dinner on one of the many outdoor patios in the neighborhood, check out a comedy show, or go bar-hopping with friends on Wells Street. If drama is more your cup of tea, catch a play at any of the theaters right down the street from The Second City.

The Perfect Sunday

Just a few blocks west of the popular North Avenue Beach, the perfect Sunday in Old Town is probably spent outdoors. The neighborhood is also home to a number of upscale boutiques and beautiful parks, so you can’t go wrong with an impromptu Sunday stroll.

Transportation Options

The Red Line, Brown Line, and Purple Line all run through Old Town, making it easy to jet down to an office in the Loop or head north to cheer on the Cubs at Wrigley Field. A bevy of bus routes also can also carry you in any direction you desire with the main east/west lines running along Division Street, which is on the south side of the neighborhood, and North Avenue, which is closer to Lincoln Park. The neighborhood is generally pedestrian friendly, while its proximity to Lincoln Park and the Lakefront Trail encourage cycling. Street parking is certainly easier to come by than in Downtown neighborhoods, but it can still be a challenge to find a spot on main streets during peak hours. Be warned that driving home from the Loop during rush hour can take three times longer than it should, as Downtown traffic tends to spill into the neighborhood, making locals thankful for that Brown Line!

Living Here

Locals Love

Unique Architecture • Entertainment Options • Central Location

Residents Say

My favorite part of Old Town is how close you can live to amazing shops, restaurants, and fun activities, while at the same time feeling like you are off the beaten path. I live one block from Lincoln Park and down the street from Second City and all of the Wells Street restaurants; however, my street is still relatively quiet and quaint. When my windows are open I hear absolutely nothing, which is rare to find in such a large city.
- Old Town Resident

Homes for Sale

Think Old Town might be the right neighborhood for you?

There are plenty of potential dream homes for sale!

View Listings in Old Town

Chicago - North Side

Old Town

Where charm meets convenience

Lincoln Park

Big nature in the big city


Wrigleyville is calling

Roscoe Village

A village within a city

North Center

New brews in an old town


Feels like family

Buena Park

A peaceful pocket on the lake


The tune of old Chicago


Bargain-priced lakeside living


Chicago's Scandinavian secret

Rogers Park

Established but evolving

West Ridge

Suburban in a good way

We've just released an update for neighborhoods.com!  You can click here to refresh and use the latest version.